Oxidative arylation of isochroman

Soo J. Park; Jason R. Price; Matthew H. Todd

doi:10.1021/jo2021373

Oxidative arylation of isochroman

Soo J. Park, Jason R. Price, Matthew H. Todd

Research output: Contribution to journal › Article › peer-review

92 Citations (Scopus)

Abstract

We report the use of a previously intractable nucleophile, anisole, in an oxidative "cross-dehydrogenative coupling" (CDC) reaction with the cyclic ether isochroman, as well as derivatives of both components. Metal catalysis was required for the reaction to proceed efficiently, and the reaction is highly sensitive to modification of either coupling partner but is able to produce a range of novel compounds via what is a synthetic alternative to the traditional oxa-Pictet―Spengler reaction.

Original language	English
Pages (from-to)	949-955
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	77
Issue number	2
DOIs	https://doi.org/10.1021/jo2021373
Publication status	Published - 2012
Externally published	Yes

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title = "Oxidative arylation of isochroman",

abstract = "We report the use of a previously intractable nucleophile, anisole, in an oxidative {"}cross-dehydrogenative coupling{"} (CDC) reaction with the cyclic ether isochroman, as well as derivatives of both components. Metal catalysis was required for the reaction to proceed efficiently, and the reaction is highly sensitive to modification of either coupling partner but is able to produce a range of novel compounds via what is a synthetic alternative to the traditional oxa-Pictet―Spengler reaction.",

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AU - Todd, Matthew H.

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AB - We report the use of a previously intractable nucleophile, anisole, in an oxidative "cross-dehydrogenative coupling" (CDC) reaction with the cyclic ether isochroman, as well as derivatives of both components. Metal catalysis was required for the reaction to proceed efficiently, and the reaction is highly sensitive to modification of either coupling partner but is able to produce a range of novel compounds via what is a synthetic alternative to the traditional oxa-Pictet―Spengler reaction.

U2 - 10.1021/jo2021373

DO - 10.1021/jo2021373

M3 - Article

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SN - 0022-3263

VL - 77

SP - 949

EP - 955

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

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Oxidative arylation of isochroman

Abstract

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